(2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-3-hydroxy-N-(pyridin-3-yl-methyl)-butyramide | 639839-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-3-hydroxy-N-(pyridin-3-yl-methyl)-butyramide
• CAS: 639839-20-6
• 化学式: C₂₄H₂₆BrN₃O₃
• 分子量: 484.393
• InChiKey: ANAWXZZMRRHMIT-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.48
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  CBZ-L-缬氨酸 、 (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-3-hydroxy-N-(pyridin-3-yl-methyl)-butyramide 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  New inhibitors of the malaria aspartyl proteases plasmepsin I and II

  摘要：

  New inhibitors of plasmepsin I and II, the aspartic proteases of the malaria parasite Plasmodium falciparum, are described. From paralell solution phase chemistry, several reversed-statine type isostere inhibitors, many of which are aza-peptides, have been prepared. The synthetic strategy delivers the target compounds in good to high overall yields and with excellent stereochemical control throughout the developed route. The final products were tested for their plasmepsin I and 11 inhibiting properties and were found to exhibit modest but promising activity. The best inhibitor exhibits K-i values of 250 nM and 1.4 muM for Plm I and II, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00312-2
• 作为产物：
  描述：

  (2R,3R)-2-(4-Bromo-benzyloxy)-3,4-dihydroxy-N-pyridin-3-ylmethyl-butyramide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 生成 (2R,3R)-4-benzylamino-2-(4-bromobenzyloxy)-3-hydroxy-N-(pyridin-3-yl-methyl)-butyramide
  参考文献：
  名称：

  New inhibitors of the malaria aspartyl proteases plasmepsin I and II

  摘要：

  New inhibitors of plasmepsin I and II, the aspartic proteases of the malaria parasite Plasmodium falciparum, are described. From paralell solution phase chemistry, several reversed-statine type isostere inhibitors, many of which are aza-peptides, have been prepared. The synthetic strategy delivers the target compounds in good to high overall yields and with excellent stereochemical control throughout the developed route. The final products were tested for their plasmepsin I and 11 inhibiting properties and were found to exhibit modest but promising activity. The best inhibitor exhibits K-i values of 250 nM and 1.4 muM for Plm I and II, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00312-2